This invention relates to low molecular weight olefin polymers and copolymers of 3-butene-1-ol, to a method for their preparation, and to their use as cosurfactants in crude oil recovery with micellar solutions.
Low molecular weight olefin polymers and copolymers of 3-butene-1-ol have not been previously known.
Photochemical reactions of olefins with ketones are known to result in cycloadditions. De Mayo, et al., Can. J. Chem., 46, 2535-2547, teaches photochemical cycloaddition of cyclopentenone to a number of olefins. De Mayo indicated (p. 2538) that yield of desired cycloaddition product might depend on the concentration of cyclopentenone and that presumably at high enough concentration dimerization might become a competitive process. De Mayo however indicated cyclohexene dimer could not be detected in the cyclopentenone cycloaddition. Evidence suggested cyclopentenone reacts photochemically from two triplet states but only the higher leads to cycloaddition. Barltrop, et al., J. Chem. Soc., D 1970 (23), 1637-8 (CA74:31374g) teaches photocycloaddition of alkyl ketones to conjugated dienes, i.e., ultraviolet irradiation of acetone and conjugated dienes such as butadiene gave vinyloxetanes by a mechanism involving the singlet excited state of the ketone. H. A. Carless, Tetrahedron Letters, 34, pp. 3173-3174, teaches that ultraviolet irradiation of acetone in the presence of olefins (2-methylpropene, 2-methylbut-2-ene or but-2-ene) leads to oxetanes as the major photoproducts.
In the absence of ultraviolet radiation, Boyce, et al., J. Chem. Soc., Perkins Trans. 1 1974 (7) 792-6 (CA81:63247d) teaches 1,1-diphenyl alkenes with carbonyl compounds underwent addition reactions exclusively at carbon-3, e.g., (C.sub.6 H.sub.5).sub.2 C.dbd.CHCH.sub.2 CH.sub.3 with (C.sub.6 H.sub.5).sub.2 CO gave (C.sub.6 H.sub.5).sub.2 C.dbd.CHCH.sub.2 CH.sub.2 C(OH)(C.sub.6 H.sub.5).sub.2. U.S. Pat. No. 3,324,187 teaches a process for preparing fluorine-substituted olefinic alcohols by mixing under substantially anhydrous conditions a fluorine-substituted, perhalogenated acetone with an alpha-olefin having at least three carbon atoms in the olefinic chain. The resulting olefinic alcohols can be halogen substituted 3-butene-1-ol monomer compounds.
Accordingly, photochemical reactions of olefins with ketones to produce cycloaddition products are known, as well as non-photochemical reactions of ketones with olefins to produce 3-butene-1-ol monomers. However, photochemical reaction of aliphatic and alicyclic ketones with aliphatic ketones to produce low molecular weight 3-butene-1-ol olefin polymers and copolymers has not been known previously.
It is therefore an object of this invention to provide a process for preparation of low molecular weight 3-butene-1-ol olefin polymers and copolymers of molecular weight range from about 200 to about 4000 and a novel class of 3-butene polyhydroxy polymers and copolymers. Other objects and advantages will become apparent as the following description proceeds.